N,N-Bis(diphenyl-phosphanyl)cyclo-propyl-amine.

In the title compound, C(27)H(25)NP(2), the diphenyl-phosphino groups are staggered relative to the PNP backbone. The dihedral angles between the phenyl rings bonded to each P atom are 51.74 (5) and 68.23 (4)°. The coordination around the N atom deviates from trigonal-pyrimidal geometry towards an almost planar arrangement between the N atom and the adjacent P and C atoms; the distance between the N atom and the plane formed by the adjacent C/P/P atoms is 0.098 (2) Å.

Related literature

For similar non-coordinated diphosphineamine ligands with distorted trigonal-pyramidal geometries see: Fei et al. (2003 ▶); Keat et al. (1981 ▶); Cotton et al. (1996 ▶); Cloete et al. (2008 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C27H25NP2

M = 425.42

Monoclinic,

a = 14.460 (4) Å

b = 10.486 (5) Å

c = 17.053 (5) Å

β = 119.358 (5)°

V = 2253.6 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.33 × 0.18 × 0.16 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.935, T max = 0.968

33310 measured reflections

5581 independent reflections

4477 reflections with I > 2.0σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.06

5581 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041711/pv2338sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041711/pv2338Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H25NP2	F(000) = 896
Mr = 425.42	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 8432 reflections
a = 14.460 (4) Å	θ = 2.5–27.5°
b = 10.486 (5) Å	µ = 0.21 mm−1
c = 17.053 (5) Å	T = 100 K
β = 119.358 (5)°	Cuboid, colourless
V = 2253.6 (15) Å3	0.33 × 0.18 × 0.16 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	5581 independent reflections
Radiation source: fine-focus sealed tube	4477 reflections with I > 2.0σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 28.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→19
Tmin = 0.935, Tmax = 0.968	k = −10→13
33310 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0466P)2 + 1.0215P] where P = (Fo2 + 2Fc2)/3
5581 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 1407 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 99.3% completeness accomplished. Spectroscopy data: 1H NMR (300 MHz, CD2Cl2): δ = 0.3 to 0.7 (m, 4H, 2 x CH2), 2.6 (m, 1H, CH), 7.3 to 7.5 (m, 20H, Ar); 31P NMR (121 MHz, CD2Cl2): δ = 63.4 (s).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.59558 (12)	0.25225 (15)	0.55966 (10)	0.0209 (3)
H1	0.5473	0.1995	0.5729	0.025*
C2	0.54277 (14)	0.32353 (16)	0.47190 (11)	0.0267 (4)
H2A	0.4654	0.3121	0.4327	0.032*
H2B	0.5833	0.3354	0.4396	0.032*
C3	0.58012 (14)	0.39375 (16)	0.55920 (11)	0.0274 (4)
H3A	0.6436	0.4488	0.5804	0.033*
H3B	0.5256	0.4255	0.5735	0.033*
C11	0.71357 (12)	0.07960 (14)	0.74371 (10)	0.0184 (3)
C12	0.63529 (12)	−0.00544 (14)	0.68578 (11)	0.0211 (3)
H12	0.6151	−0.0062	0.6237	0.025*
C13	0.58661 (13)	−0.08882 (16)	0.71768 (11)	0.0248 (3)
H13	0.5327	−0.145	0.6773	0.03*
C14	0.61675 (14)	−0.08999 (16)	0.80836 (12)	0.0258 (4)
H14	0.5834	−0.1467	0.8303	0.031*
C15	0.69601 (13)	−0.00792 (15)	0.86719 (11)	0.0245 (3)
H15	0.7173	−0.0093	0.9295	0.029*
C16	0.74413 (13)	0.07601 (15)	0.83527 (11)	0.0213 (3)
H16	0.7984	0.1316	0.876	0.026*
C21	0.77084 (12)	0.33887 (14)	0.75153 (10)	0.0180 (3)
C22	0.68675 (13)	0.37085 (15)	0.76614 (10)	0.0205 (3)
H22	0.635	0.3084	0.7576	0.025*
C23	0.67822 (14)	0.49346 (15)	0.79308 (11)	0.0251 (3)
H23	0.6203	0.5145	0.8022	0.03*
C24	0.75390 (14)	0.58542 (16)	0.80678 (11)	0.0258 (4)
H24	0.7471	0.6694	0.8242	0.031*
C25	0.83918 (14)	0.55410 (15)	0.79498 (11)	0.0241 (3)
H25	0.8921	0.616	0.8057	0.029*
C26	0.84747 (13)	0.43169 (15)	0.76732 (10)	0.0207 (3)
H26	0.9061	0.4109	0.7591	0.025*
C31	0.76517 (12)	−0.03248 (14)	0.55113 (10)	0.0182 (3)
C32	0.68867 (13)	−0.12527 (15)	0.50250 (11)	0.0222 (3)
H32	0.6234	−0.1006	0.4519	0.027*
C33	0.70678 (14)	−0.25267 (15)	0.52714 (11)	0.0262 (4)
H33	0.654	−0.3147	0.4938	0.031*
C34	0.80162 (14)	−0.28923 (15)	0.60026 (12)	0.0272 (4)
H34	0.8142	−0.3766	0.6168	0.033*
C35	0.87866 (14)	−0.19906 (15)	0.64963 (12)	0.0269 (4)
H35	0.9436	−0.2245	0.7002	0.032*
C36	0.86059 (13)	−0.07105 (15)	0.62481 (11)	0.0223 (3)
H36	0.9137	−0.0095	0.6583	0.027*
C41	0.85308 (12)	0.20398 (14)	0.53650 (10)	0.0173 (3)
C42	0.91036 (12)	0.14796 (15)	0.49881 (10)	0.0201 (3)
H42	0.8889	0.0675	0.4699	0.024*
C43	0.99796 (13)	0.20875 (16)	0.50336 (11)	0.0239 (3)
H43	1.0358	0.1699	0.4772	0.029*
C44	1.03073 (13)	0.32609 (16)	0.54587 (12)	0.0267 (4)
H44	1.0911	0.3672	0.5492	0.032*
C45	0.97516 (14)	0.38290 (15)	0.58346 (12)	0.0266 (4)
H45	0.9978	0.4628	0.6131	0.032*
C46	0.88620 (13)	0.32314 (14)	0.57785 (11)	0.0222 (3)
H46	0.8474	0.3638	0.6024	0.027*
N1	0.70166 (10)	0.20116 (11)	0.59277 (8)	0.0171 (3)
P1	0.78650 (3)	0.18492 (4)	0.70717 (3)	0.01690 (10)
P2	0.72688 (3)	0.13260 (4)	0.51349 (3)	0.01718 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (7)	0.0222 (8)	0.0204 (8)	0.0035 (6)	0.0094 (6)	−0.0003 (6)
C2	0.0286 (9)	0.0274 (8)	0.0215 (8)	0.0078 (7)	0.0101 (7)	0.0011 (7)
C3	0.0304 (9)	0.0247 (8)	0.0227 (8)	0.0083 (7)	0.0097 (7)	0.0006 (7)
C11	0.0196 (7)	0.0158 (7)	0.0213 (8)	0.0023 (6)	0.0112 (6)	0.0005 (6)
C12	0.0254 (8)	0.0202 (7)	0.0193 (8)	−0.0002 (6)	0.0124 (7)	−0.0017 (6)
C13	0.0272 (9)	0.0216 (8)	0.0261 (9)	−0.0058 (6)	0.0135 (7)	−0.0045 (7)
C14	0.0304 (9)	0.0222 (8)	0.0306 (9)	−0.0029 (7)	0.0194 (8)	0.0013 (7)
C15	0.0301 (9)	0.0257 (8)	0.0203 (8)	0.0007 (7)	0.0142 (7)	0.0019 (6)
C16	0.0227 (8)	0.0202 (7)	0.0196 (8)	−0.0014 (6)	0.0092 (6)	−0.0003 (6)
C21	0.0208 (8)	0.0186 (7)	0.0134 (7)	0.0010 (6)	0.0073 (6)	0.0002 (6)
C22	0.0220 (8)	0.0209 (7)	0.0187 (8)	−0.0005 (6)	0.0102 (6)	−0.0007 (6)
C23	0.0283 (9)	0.0251 (8)	0.0244 (8)	0.0051 (7)	0.0148 (7)	−0.0007 (7)
C24	0.0362 (9)	0.0186 (7)	0.0209 (8)	0.0025 (7)	0.0127 (7)	−0.0009 (6)
C25	0.0315 (9)	0.0206 (8)	0.0186 (8)	−0.0048 (7)	0.0112 (7)	−0.0011 (6)
C26	0.0227 (8)	0.0229 (8)	0.0165 (7)	−0.0022 (6)	0.0097 (6)	−0.0011 (6)
C31	0.0225 (8)	0.0173 (7)	0.0216 (8)	−0.0009 (6)	0.0161 (7)	−0.0015 (6)
C32	0.0253 (8)	0.0222 (8)	0.0232 (8)	−0.0029 (6)	0.0150 (7)	−0.0034 (6)
C33	0.0365 (10)	0.0211 (8)	0.0279 (9)	−0.0086 (7)	0.0210 (8)	−0.0066 (7)
C34	0.0413 (10)	0.0162 (7)	0.0311 (9)	−0.0017 (7)	0.0233 (8)	0.0003 (7)
C35	0.0289 (9)	0.0238 (8)	0.0286 (9)	0.0024 (7)	0.0146 (7)	0.0052 (7)
C36	0.0226 (8)	0.0192 (7)	0.0270 (8)	−0.0018 (6)	0.0136 (7)	−0.0008 (6)
C41	0.0200 (7)	0.0178 (7)	0.0147 (7)	0.0011 (6)	0.0088 (6)	0.0038 (6)
C42	0.0241 (8)	0.0178 (7)	0.0198 (8)	0.0027 (6)	0.0118 (7)	0.0018 (6)
C43	0.0246 (8)	0.0263 (8)	0.0264 (8)	0.0054 (6)	0.0169 (7)	0.0078 (7)
C44	0.0248 (8)	0.0280 (8)	0.0291 (9)	−0.0039 (7)	0.0147 (7)	0.0077 (7)
C45	0.0343 (9)	0.0196 (8)	0.0255 (9)	−0.0068 (7)	0.0143 (8)	0.0001 (6)
C46	0.0308 (9)	0.0178 (7)	0.0224 (8)	−0.0005 (6)	0.0164 (7)	0.0010 (6)
N1	0.0179 (6)	0.0186 (6)	0.0155 (6)	0.0020 (5)	0.0088 (5)	−0.0004 (5)
P1	0.0173 (2)	0.01718 (19)	0.0168 (2)	0.00046 (14)	0.00886 (16)	−0.00058 (14)
P2	0.0189 (2)	0.01685 (19)	0.0170 (2)	0.00047 (14)	0.00976 (16)	−0.00097 (14)

C1—N1	1.452 (2)	C25—C26	1.393 (2)
C1—C3	1.500 (2)	C25—H25	0.95
C1—C2	1.504 (2)	C26—H26	0.95
C1—H1	1	C31—C36	1.395 (2)
C2—C3	1.504 (2)	C31—C32	1.399 (2)
C2—H2A	0.99	C31—P2	1.8349 (17)
C2—H2B	0.99	C32—C33	1.386 (2)
C3—H3A	0.99	C32—H32	0.95
C3—H3B	0.99	C33—C34	1.380 (3)
C11—C12	1.399 (2)	C33—H33	0.95
C11—C16	1.399 (2)	C34—C35	1.387 (2)
C11—P1	1.8342 (16)	C34—H34	0.95
C12—C13	1.390 (2)	C35—C36	1.393 (2)
C12—H12	0.95	C35—H35	0.95
C13—C14	1.386 (2)	C36—H36	0.95
C13—H13	0.95	C41—C46	1.399 (2)
C14—C15	1.390 (2)	C41—C42	1.402 (2)
C14—H14	0.95	C41—P2	1.8282 (16)
C15—C16	1.388 (2)	C42—C43	1.386 (2)
C15—H15	0.95	C42—H42	0.95
C16—H16	0.95	C43—C44	1.388 (2)
C21—C22	1.396 (2)	C43—H43	0.95
C21—C26	1.398 (2)	C44—C45	1.384 (2)
C21—P1	1.8433 (17)	C44—H44	0.95
C22—C23	1.391 (2)	C45—C46	1.391 (2)
C22—H22	0.95	C45—H45	0.95
C23—C24	1.390 (2)	C46—H46	0.95
C23—H23	0.95	N1—P2	1.7208 (13)
C24—C25	1.383 (2)	N1—P1	1.7301 (14)
C24—H24	0.95
N1—C1—C3	119.55 (14)	C26—C25—H25	120
N1—C1—C2	119.64 (14)	C25—C26—C21	121.00 (15)
C3—C1—C2	60.09 (11)	C25—C26—H26	119.5
N1—C1—H1	115.5	C21—C26—H26	119.5
C3—C1—H1	115.5	C36—C31—C32	118.53 (14)
C2—C1—H1	115.5	C36—C31—P2	125.74 (12)
C1—C2—C3	59.83 (11)	C32—C31—P2	115.68 (12)
C1—C2—H2A	117.8	C33—C32—C31	120.89 (16)
C3—C2—H2A	117.8	C33—C32—H32	119.6
C1—C2—H2B	117.8	C31—C32—H32	119.6
C3—C2—H2B	117.8	C34—C33—C32	119.85 (15)
H2A—C2—H2B	114.9	C34—C33—H33	120.1
C1—C3—C2	60.07 (11)	C32—C33—H33	120.1
C1—C3—H3A	117.8	C33—C34—C35	120.37 (15)
C2—C3—H3A	117.8	C33—C34—H34	119.8
C1—C3—H3B	117.8	C35—C34—H34	119.8
C2—C3—H3B	117.8	C34—C35—C36	119.81 (16)
H3A—C3—H3B	114.9	C34—C35—H35	120.1
C12—C11—C16	118.33 (14)	C36—C35—H35	120.1
C12—C11—P1	123.02 (12)	C35—C36—C31	120.55 (15)
C16—C11—P1	118.40 (12)	C35—C36—H36	119.7
C13—C12—C11	120.96 (15)	C31—C36—H36	119.7
C13—C12—H12	119.5	C46—C41—C42	118.17 (14)
C11—C12—H12	119.5	C46—C41—P2	122.20 (12)
C14—C13—C12	119.98 (15)	C42—C41—P2	118.81 (12)
C14—C13—H13	120	C43—C42—C41	120.72 (15)
C12—C13—H13	120	C43—C42—H42	119.6
C13—C14—C15	119.78 (15)	C41—C42—H42	119.6
C13—C14—H14	120.1	C42—C43—C44	120.36 (15)
C15—C14—H14	120.1	C42—C43—H43	119.8
C16—C15—C14	120.26 (15)	C44—C43—H43	119.8
C16—C15—H15	119.9	C45—C44—C43	119.75 (15)
C14—C15—H15	119.9	C45—C44—H44	120.1
C15—C16—C11	120.65 (15)	C43—C44—H44	120.1
C15—C16—H16	119.7	C44—C45—C46	120.09 (15)
C11—C16—H16	119.7	C44—C45—H45	120
C22—C21—C26	118.40 (14)	C46—C45—H45	120
C22—C21—P1	125.20 (12)	C45—C46—C41	120.89 (15)
C26—C21—P1	116.33 (12)	C45—C46—H46	119.6
C23—C22—C21	120.45 (15)	C41—C46—H46	119.6
C23—C22—H22	119.8	C1—N1—P2	116.03 (10)
C21—C22—H22	119.8	C1—N1—P1	120.30 (10)
C24—C23—C22	120.45 (16)	P2—N1—P1	122.58 (8)
C24—C23—H23	119.8	N1—P1—C11	103.56 (7)
C22—C23—H23	119.8	N1—P1—C21	102.40 (7)
C25—C24—C23	119.71 (15)	C11—P1—C21	100.43 (7)
C25—C24—H24	120.1	N1—P2—C41	103.54 (7)
C23—C24—H24	120.1	N1—P2—C31	105.26 (7)
C24—C25—C26	119.94 (15)	C41—P2—C31	102.29 (7)
C24—C25—H25	120
N1—C1—C2—C3	−109.10 (16)	C44—C45—C46—C41	1.6 (2)
N1—C1—C3—C2	109.25 (16)	C42—C41—C46—C45	−1.6 (2)
C16—C11—C12—C13	2.0 (2)	P2—C41—C46—C45	−171.14 (12)
P1—C11—C12—C13	176.10 (12)	C3—C1—N1—P2	−111.08 (14)
C11—C12—C13—C14	−1.1 (2)	C2—C1—N1—P2	−40.77 (18)
C12—C13—C14—C15	−0.3 (3)	C3—C1—N1—P1	80.49 (16)
C13—C14—C15—C16	0.7 (3)	C2—C1—N1—P1	150.80 (12)
C14—C15—C16—C11	0.2 (2)	C1—N1—P1—C11	58.57 (13)
C12—C11—C16—C15	−1.5 (2)	P2—N1—P1—C11	−109.08 (9)
P1—C11—C16—C15	−175.91 (12)	C1—N1—P1—C21	−45.54 (13)
C26—C21—C22—C23	1.9 (2)	P2—N1—P1—C21	146.81 (9)
P1—C21—C22—C23	−174.81 (12)	C12—C11—P1—N1	24.39 (14)
C21—C22—C23—C24	−0.7 (2)	C16—C11—P1—N1	−161.48 (12)
C22—C23—C24—C25	−1.1 (2)	C12—C11—P1—C21	129.99 (13)
C23—C24—C25—C26	1.6 (2)	C16—C11—P1—C21	−55.87 (13)
C24—C25—C26—C21	−0.3 (2)	C22—C21—P1—N1	79.58 (14)
C22—C21—C26—C25	−1.4 (2)	C26—C21—P1—N1	−97.23 (12)
P1—C21—C26—C25	175.60 (12)	C22—C21—P1—C11	−26.95 (15)
C36—C31—C32—C33	0.4 (2)	C26—C21—P1—C11	156.23 (12)
P2—C31—C32—C33	−177.16 (12)	C1—N1—P2—C41	131.82 (11)
C31—C32—C33—C34	−0.4 (2)	P1—N1—P2—C41	−60.04 (10)
C32—C33—C34—C35	0.5 (3)	C1—N1—P2—C31	−121.16 (11)
C33—C34—C35—C36	−0.6 (3)	P1—N1—P2—C31	46.98 (10)
C34—C35—C36—C31	0.6 (2)	C46—C41—P2—N1	−25.59 (14)
C32—C31—C36—C35	−0.5 (2)	C42—C41—P2—N1	164.95 (12)
P2—C31—C36—C35	176.77 (12)	C46—C41—P2—C31	−134.83 (13)
C46—C41—C42—C43	0.6 (2)	C42—C41—P2—C31	55.71 (13)
P2—C41—C42—C43	170.51 (12)	C36—C31—P2—N1	−71.90 (15)
C41—C42—C43—C44	0.4 (2)	C32—C31—P2—N1	105.44 (12)
C42—C43—C44—C45	−0.4 (2)	C36—C31—P2—C41	36.03 (15)
C43—C44—C45—C46	−0.6 (3)	C32—C31—P2—C41	−146.64 (12)